36-Dimethoxybenzocyclobutenone: a reagent for quinone synthesis
M Azadi-Ardakani, TW Wallace
Index: Azadi-Ardakani, Manouchehr; Wallace, Timothy W. Tetrahedron, 1988 , vol. 44, # 18 p. 5939 - 5952
Full Text: HTML
Citation Number: 38
Abstract
3, 6-Dimethoxybenzocyclobutenone 4 is prepared in four efficient steps from 2, 5- dimethoxybenzoic acid 8. The derived benzocyclobutenol 13 undergoes electrocyclic ring opening at 110–115° C to give the hydroxy-o-quinone dimethide 21, which reacts with dienophiles to give 5, 8-dimethoxy-1, 2, 3, 4-tetrahydro-1-naphthol derivadves stereoselecdvely. Since the ketone 4 can be functionalised at C-5 using electrophiles and ...
Related Articles:
The first total synthesis and structural determination of antibiotics K1115 B 1 s (alnumycins)
[Tatsuta, Kuniaki; Tokishita, Sonoko; Fukuda, Tomohiro; Kano, Takaaki; Komiya, Tadaaki; Hosokawa, Seijiro Tetrahedron Letters, 2011 , vol. 52, # 9 p. 983 - 986]
Synthesis of aromatic carbonyl compounds via thallation-carbonylation of arenes
[Larock, Richard C.; Fellows, Constance A. Journal of the American Chemical Society, 1982 , vol. 104, # 7 p. 1900 - 1907]